Middletown is a city in Orange County, New York, United States. It lies in New York's Hudson Valley region, near the Wallkill River and the foothills of the Shawangunk Mountains. Middletown is situated between Port Jervis and Newburgh, New York. As of the 2010 United States Census, the city's population was 28,086, reflecting an increase of 2,698 from the 25,388 counted in the 2000 Census.